Fluoromethyl ketones and liquid-crystalline media

• US 5,458,806 A
• Filed: 05/04/1994
• Issued: 10/17/1995
• Est. Priority Date: 01/22/1993
• Status: Expired due to Fees

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Plach, Herbert, Bartmann, Ekkehard
• Primary Examiner(s): KELLY, CYNTHIA HARRIS
• Application Number:
  US08/238,087
• Time in Patent Office: 531 Days
• Field of Search: 252/299.63, 252/299.66, 252/299.62, 252/299.61, 544/298, 549/369, 549/370, 570/129, 570/144, 546/339, 560/65, 560/100, 560/102, 568/308, 568/335
• US Class Current: 252/299.63
• CPC Class Codes: C07C 49/813 polycyclic
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 213/50 Ketonic radicals
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C09K 19/0403 the structure containing one or more specific, optionally substituted ring or ring systems
• CPC Class Codes: C09K 19/12 at least two benzene rings directly linked, e.g. biphenyls
• CPC Class Codes: C09K 19/3003 Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
• CPC Class Codes: C09K 19/3028 in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
• CPC Class Codes: C09K 19/3402 having oxygen as hetero atom sugars C09K19/0422
• CPC Class Codes: C09K 19/3444 the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 2019/0407 containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
• CPC Class Codes: C09K 2019/0444 characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
• CPC Class Codes: C09K 2019/3021 Cy-Ph-Ph-Cy
• CPC Class Codes: C09K 2019/3422 the heterocyclic ring being a six-membered ring

Abstract

Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,

A¹ and A² are each, independently of one another, a

(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH₂ groups is optionally replaced by --O-- and/or --S--,

(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or

(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,

wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,

Z¹ and Z² are each, independently of one another, --CO--O--, --O--CO--, --CH₂ O--, --OCH₂ --, --CH₂ CH₂ --, --CH═CH--, --C.tbd.C-- or a single bond, and one of the radicals Z¹ and Z² is optionally --(CH₂)₄ -- or --CH═CH--CH₂ CH₂ --,

X is H, F or Cl and

is 0, 1 or 2.

Claims

1. Fluoromethyl ketones of the formula I ##STR159## in which R is H, an alkyl or alkenyl radical having 1 to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF₃ or substituted by halogen, and one or more CH₂ groups in these radicals is optionally replaced, in each case independently of one another, by --O--, --S--, ##STR160## --CO--, --CO--O--, --O--CO-- or --O--CO--O--, in such a way that O atoms are not linked directly to one another,

A¹ and A² are each, independently of one another, a

(a) trans-1,4-cyclohexylene radical in which, in addition, one or more non-adjacent CH₂ groups is optionally replaced by --O-- and/or --S--,

(b) 1,4-phenylene radical in which, in addition, one or two CH groups is optionally replaced by N, or

(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,

wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,

Z¹ and Z² are each, independently of one another, --CO--O--, --O--CO--, --CH.sub. O--, --OCH₂ --, --CH₂ CH₂ --, --CH═

CH--, --C.tbd.C-- or a single bond, and one of the radicals Z¹ and Z² is optionally --(CH₂)₄ -- or --CH═

CH--CH₂ CH₂ --,

X is H, F or Cl and

m is 0, 1 or 2.

2. Compounds of the formula I1, ##STR161## in which R and X are as defined in claim 1.

3. Compounds of the formula I3, ##STR162## in which R and X are as defined in claim 1.

4. Compounds of the formula I4, ##STR163## in which R and X are as defined in claim 1.

5. Compounds of the formula I5, ##STR164## in which R and X are as defined in claim 1.

6. Compounds according to claim 1, wherein X is fluorine.

7. A method of using compounds of claim 1 as components of liquid-crystalline media which comprises adding said compounds to a liquid-crystalline medium.

8. Liquid-crystalline medium having at least two liquid-crystalline components, which contains at least one compound of the formula I ##STR165## wherein R, A¹, A², Z¹, Z², X and m are as defined in claim 1.

9. Liquid-crystalline medium according to claim 8, characterized in that it additionally contains one or more compounds selected from the group consisting of the general formulae II, III and IV:

##STR166## in which the individual radicals have the following meanings;

R'"'"';

alkyl, oxaalkyl, fluoroalkyl or alkenyl, in each case having up to 7 carbon atoms,

X'"'"';

F, Cl, CF₃, OCF₃ or OCHF₂,

Y'"'"' and Z;

each, independently of another, H or F, and

r;

0 or 1.

10. Liquid-crystal display element, characterized in that it contains a liquid-crystalline medium according to claim 8.

11. Electro-optical display element, characterized in that it contains, as dielectric, a liquid-crystalline medium according to claim 8.